Ethanol → HCID 17989196, compound

HRID 420635Notes

Reaction equation

HRID 420635 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])=[C:4]([O:17][CH3:18])[C:3]=1[F:19].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:30](O)[CH3:31]>>[CH2:30]([O:12][C:11](=[O:13])[C:10](=[O:14])[CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:19])[C:4]=1[O:17][CH3:18])([CH3:16])[CH3:15])[CH3:31]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 17989224HCID 17989224, compound

Product 1

HCID 17989196HCID 17989196, compound

Procedure

5.44 g (18.84 mmol) of 4-(4-chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-oxo-pentanoic acid is dissolved in 117 ml of ethanol, mixed with 2.1 ml of concentrated sulfuric acid and refluxed for six hours. The reaction mixture is added to 250 ml of saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic extracts are washed with saturated sodium bicarbonate solution and with brine. After drying and after the desiccant is filtered off and the solvent is spun in, 5.19 g (87%) of the desired compound is obtained.

Workup

  1. temperaturerefluxed for six hours
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with saturated sodium bicarbonate solution and with brine
  4. customAfter drying
  5. filtrationafter the desiccant is filtered off
  6. customis obtained

Sources & evidence

ORD record
ord-3f32954e06b548db88dd422c8f9ddaa3
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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